[Br:1][C:2]1[CH:9]=[CH:8][C:5](C=C)=[CH:4][CH:3]=1.C[N+]1([O-])[CH2:16][CH2:15][O:14]CC1.CC(C)=[O:20].O>CCOC(C)=O.[Os](=O)(=O)(=O)=O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:15]([OH:14])[CH2:16][OH:20])=[CH:4][CH:3]=14-Bromostyrene (1.00 g, 5.46 mmol) was dissolved in 25 mls of 2:1 water acetone. To this was added 4-methylmorpholine N-oxide (0.704 g, 6.01 mmole) and osmium tetroxide (0.167 g, 0.061 mmole, 2.5% in t-BuOH). This mixture was stirred at room temperature for 16 hours, then diluted with EtOAc, washed once with 1N aq. HCl, once with saturated sodium bicarbonate solution, dried over sodium sulfate and concentrated under reduced pressure. The resulting crude product was purified by Flash 40 Biotage (40M cartridge, 100% EtOAc as the eluant) to give 335 mgs (28%) of 1-(4-bromophenyl)ethane-1,2-diol as a white solid.
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